Designing amorphous formulations of polyphenols with naringin by spray-drying for enhanced solubility and permeability

Naringin (NAR), a major flavanone (FVA) glycoside, is a component of food mainly obtained from grapefruit. We used NAR as a food additive to improve the solubility and permeability of hydrophobic polyphenols used as supplements in the food industry. The spray-dried particles (SDPs) of NAR alone show an amorphous state with a glass transition temperature (T_g) at 93.2 °C. SDPs of hydrophobic polyphenols, such as flavone (FVO), quercetin (QCT), naringenin (NRG), and resveratrol (RVT) were prepared by adding varying amounts of NAR. All SDPs of hydrophobic polyphenols with added NAR were in an amorphous state with a single T_g, but SDPs of hydrophobic polyphenols without added NAR showed diffraction peaks derived from each crystal. The SDPs with NAR could keep an amorphous state after storage at a high humidity condition for one month, except for SDPs of RVT/NAR. SDPs with NAR enhanced the solubility of hydrophobic polyphenols, especially NRG solubility, which was enhanced more than 9 times compared to NRG crystal. The enhanced solubility resulted in the increased membrane permeability of NRG. The antioxidant effect of the hydrophobic NRG was also enhanced by the synergetic effect of NAR. The findings demonstrated that NAR could be used as a food additive to enhance the solubility and membrane permeability of hydrophobic polyphenols.     

Antioxidant properties,radical scavenging activity and biomolecule protection capacity of flavonoid naringenin and its glycoside naringin: a comparative study

BACKGROUND: This study was designed to evaluate and compare antioxidant capacity and radical scavenging activity of naringin and its aglycone by different in vitro assays. The effects of flavanones on lipid peroxidation, glutathione (GSH) oxidation and DNA cleavage were also assessed. RESULTS: The results showed that naringenin exhibited higher antioxidant capacity and hydroxyl and superoxide radical scavenger efficiency than naringin. Our results evidenced that glycosylation attenuated the efficiency in inhibiting the enzyme xanthine oxidase and the aglycone could act like a more active chelator of metallic ions than the glycoside. Additionally, naringenin showed a greater effectiveness in the protection against oxidative damage to lipids in a dose‐dependent manner. Both flavanones were equally effective in reducing DNA damage. However, they show no protective effect on oxidation of GSH. CONCLUSION: The data obtained support the importance of characterizing the ratio naringin/naringenin in foods when they are evaluated for their health benefits. Copyright © 2010 Society of Chemical Industry     

柚皮苷-卵磷脂包合物的制备及其理化性质研究

柚皮苷是一种天然抗氧化剂,具有多种生物活性,但是存在脂溶性差、口服吸收率低等问题。为了提高柚皮苷的脂溶性和生物利用度,本研究制备了柚皮苷-卵磷脂包合物,并采用紫外(UV),红外(IR),差示量热扫描(DSC),X-射线衍射(XRD)等波谱分析方法研究了该包合物的理化性质。研究结果表明,柚皮苷与卵磷脂并没有形成一种新的化合物,柚皮苷只是以一种无定形状态分散在卵磷脂中,二者是通过氢键、范德华力等非共价键形式相结合。同时对比了柚皮苷与柚皮苷-卵磷脂包合物中柚皮苷在正辛醇中的溶解性,结果表明,与卵磷脂形成包合物后,柚皮苷在正辛醇中的溶解度由3.28μg/m L增加至755.50μg/m L,脂溶性得到了显著的提高;亚油酸体系中抗氧化能力实验表明,柚皮苷与卵磷脂的包合可以显著提高柚皮苷在脂溶性体系中的抗氧化能力。     

Debittering and Deacidifying Sour Orange (Citrus aurantium) Juice Using Neutral and Anion Exchange Resins

Juices from four cultivars of sour orange (Citrus aurantium), Seville, Bigaradier, Sour and Bittersweet, were treated with neutral (XAD-16) and weak base anionic exchange (IRA-93) resins. Unidentified fluorescent compounds were removed along with bitter compounds by both resin treatments. Average acidity was reduced from 57–87% using IRA-93 before depletion. Average naringin concentrations were reduced 50–66% in high acid juice and 89% in low acid juice using IRA-93. Under similar conditions 24–30% of the limonin was eliminated using IRA-93 and essentially 100% removed using XAD-16. Sensory acceptance (9-point hedonic scale) improved from 1.6 to 3.0 after IRA-93 resin treatment of a high acid juice. Average acceptance increased from 3.8 to 6.4 after XAD-16 treatment of a low acid juice.     

反胶团萃取柚皮苷的初步研究

反胶团萃取法是一种新型、高效的生物活性物质分离技术。通过五因素三水平的正交试验,研究反胶团体系中丁二酸-2-乙基己基酯磺酸钠(AOT)浓度、萃取pH、萃取离子强度、反萃取pH、反萃取离子强度对柚皮苷提取的影响。结果表明,萃取pH值和反萃取pH值对柚皮苷的反胶团萃取起着显著作用,因素作用的主次顺序为萃取pH值>反萃取pH值>萃取离子强度>AOT浓度>反萃取离子强度。最优提取条件为萃取pH4.0、反萃取pH10.0、萃取离子强度0.2mol/L、AOT浓度50.0mmol/L、反萃取离子强度0.5mol/L。柚皮苷的萃取率可达96.15%。     

柚皮苷的溶剂热法提取及其抗氧化性、稳定性测定

对柚皮中柚皮苷进行提取,并测定其抗氧化和稳定性。以乙醇-水混合体系为溶剂,对恩施特产贡水白柚皮中柚皮苷进行溶剂热法提取,提取的柚皮苷用紫外吸收光谱定量测定。考察乙醇体积分数、柚皮粉粒度、填充度、提取温度及提取时间对柚皮苷提取率的影响。方法的回收率为96.51%～101.9%,相对标准偏差小于0.16%。同时,采用流动注射化学发光分析测定了柚皮苷的抗氧化性能,并通过测定不同放置时间条件下样品溶液的紫外吸收光谱强度对柚皮苷的稳定性进行测定。结果表明,该溶剂热法提取柚皮苷效率较高,提取最佳工艺条件为乙醇体积分数70%、柚皮粉粒度120目、填充度80%、提取温度60℃和提取时间3h。提取出的柚皮苷具有较强的抗氧化性能和一定的稳定性。     

Chemistry of Leichhardt's Grasshopper, Petasida ephippigera, and its Host Plants, Pityrodia jamesii, P. ternifolia, and P. pungens

Investigation of the strikingly aposematic Leichhardt's grasshopper revealed a number of host-plant-derived components. Chemical study of the three known host plants revealed a diverse array of components. Pityrodia ternifolia and P. pungens contain predominantly sesquiterpenes and sesquiterpene glycosides and P. jamesii is rich in cineole, dihydrochalcones, chalcones, and monoterpene glycosides. Feces from grasshoppers feeding on P. jamesii contain a mixture of hydroxycineoles, of which 3-hydroxycineole is the predominant isomer (68%). No evidence for previously suspected "alkaloidal" toxins was found in either the insect or host plant.     

荧光磁性表面分子印迹聚合物对柚皮苷的荧光偏振检测

采用荧光磁性表面分子印迹法对柚皮苷进行荧光偏振检测。该方法以二氧化硅包裹的磁性颗粒为基质,甲基丙烯酸和丙烯酰胺为单体,并用异硫氰酸荧光素标记,得到同时具有荧光和磁性的表面分子印迹聚合物。并采用荧光偏振法和紫外分光光度法对制备的聚合物结合能力进行检测。通过与比较2种检测方法可知荧光偏振法更为灵敏,检出限为0.1?mg/L。最后对番茄酱中含有的柚皮苷进行回收率检测,回收率达到81.3%以上。说明采用荧光磁性表面分子印迹法对食品中柚皮苷可快速、高效地检测。     

强阴离子交换固相萃取柱分离纯化柚皮苷

目的：建立固相萃取分离纯化柚皮苷的方法。方法：以强阴离子交换(strong anion exchange,SAX)填料为吸附材料,利用柚皮苷与填料的功能基团之间的静电作用将柚皮苷吸附在填料上,考察洗脱液离子强度、洗脱液体积,洗脱流速对洗脱效果的影响。结果：选用5mL碳酸氢钠溶液(0.1mol/L,pH9.0)为洗脱液,以0.5mL/min的流速进行洗脱,回收率达到91%以上。结论：本方法简单、高效,选择性好,可为柚皮苷样品的纯化提供理论依据。